Formaldehyde → HCID 14618373, compound

HRID 1638502Notes

Reaction equation

[CH3:1][C:2]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[C:7]([CH:13]([CH3:15])[CH3:14])[CH:6]=1)([CH3:4])[CH3:3].[CH2:16]=[O:17].[OH-].[K+].O>CCCCCC>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH:13]([CH3:15])[CH3:14])[C:8]([OH:12])=[C:9]([CH2:16][OH:17])[C:10]=1[CH3:11])([CH3:1])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 4-(1,1-dimethylethyl)-2-(1-methylethyl)-5-methylphenol (103.2 g, 0.5 mol), 40% formaldehyde solution (375 mL, 5 mol), potassium hydroxide (49.5 g, 0.75 mol) and poly(ethylene glycol) avg. M.W. 300 (1 g) was heated at reflux for 24 hour. The mixture was cooled to 25° C. and water (1 L) and hexane (700 mL) were added. The aqueous layer was extracted with hexane (2×100 mL). The combined organic extracts were washed with water (3×100 mL), brine (2×100 mL) and dried (Na2SO4). Evaporation of solvents and crystallization of the residue from hexane gave 10.2 g (8.6% yield) of 5-(1,1-dimethylethyl)-6-methyl-3-(1-methylethyl)-2-hydroxy benzenemethanol, mp 143°-146° C.; 1H-NMR (CDCl3)δ 1.25 (6H, d, J=7 Hz), 1.40 (9H, s), 2.31 (3H, s), 3.0-3.6 (1H, m), 4.85 (2H, s), 7.01 (1H, s), 7.23 (1H, s); IR (CHCl3)νmax 3550, 3350, 2940, 1575, 1470, 1360 cm-1 ; M m/e 236, 218, 206, 203, 191, 161, UVλmax (ethanol) 224 nm (ε=6690), 287 nm (ε=2480).

Workup

temperatureat reflux for 24 hour
extractionThe aqueous layer was extracted with hexane (2×100 mL)
washThe combined organic extracts were washed with water (3×100 mL), brine (2×100 mL)
dry with materialdried (Na2SO4)
customEvaporation of solvents and crystallization of the residue from hexane

Sources & evidence

ORD record: ord-1b546a94562e4dff8efe9d1355805cb2
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04880775

Reaction notes

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