Sodium Hydroxide → 4-Hydroxymethyl-2-(2-methylphenyl)benzoic acid

HRID 2121269Notes

Reaction equation

C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18].[OH-].[Na+]>CCO>[OH:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:19])=[O:2])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-hydroxymethyl-2-(2-methylphenyl)benzoic acid methyl ester (73 g, 285 mmol), prepared as in example 1075D, in EtOH (300 mL) was added an aqueous 4N NaOH solution (350 mL, 1.4 mol), and mixture heated at 80° C. overnight. Reaction concentrated in vacuo, and residue mixed with water (300 mL). Aqueous mixture acidified to pH 6 using aqueous 3N HCl, and acid product extracted out with CHCl3 (3×200 mL). Organic extracts dried with Na2SO4, filtered, and concentrated in vacuo to produce a white solid (69 g, 100% crude yield). m/e (DCI) 243 (MH+).

Workup

customReaction
concentrationconcentrated in vacuo, and residue
additionmixed with water (300 mL)
extractionextracted out with CHCl3 (3×200 mL)
dry with materialOrganic extracts dried with Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto produce a white solid (69 g, 100% crude yield)

Sources & evidence

ORD record: ord-0a77eb75b5404b698ddddc42a2f7965c
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693123B2

Reaction notes

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