Benzene → β-Methyl-4-(2-methylpropyl)benzeneethanol

HRID 1111306Notes

Reaction equation

HRID 1111306 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([CH3:17])[CH2:12][O:13]C(=O)C)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C1C=CC=CC=1.C=O.C(C1C=CC([C@@H](C)CO)=CC=1)(C)C>C(Cl)(Cl)Cl>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:17])[CH2:12][OH:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 241BenzeneHCID 712FormaldehydeHCID 18642410HCID 18642410, compoundHCID 18642411HCID 18642411, compound

Product 1

HCID 595160β-Methyl-4-(2-methylpropyl)benzeneethanol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The following are obtained: 590 mg of (S)-2-(4- isobutyl-phenyl)-1-acetoxy-propane, as a colorless oil with [α]D20 -7.0° (C=1, benzene), ee 98%, H-NMR (90 MHz in COCl3) (ppm): 0.9 (6H, d, CHHD 3CHCHHD 3; 1.3 (3H, d, CHHD 3CH); 1.5-2.0 (1H, m, CH3CHH3); 2.1 (3H, s, COCH3 ; 2.4 (2H, d, C6H4CHHD 2); 3.1-2.7 (1H, m, C6H4CHHD 2); 4.1 (2H, d, CH2O); 7.0 (4H, s, aromatics); and 490 mg of (R)-2-(4-isopropyl-phenyl)-propan-1-ol as a colorless oil with [α]D20 +12.8° (C=1, CHCl3), ee 97%, H-NMR (90 MHz in COCl3)δ(ppm): 0.9 (6H, d, CHHD 3CHCHHD 3); 1.3 (3H, d, CHHD 3CH), 1.7-2.2 (1H, m. CH3CHH3); 2.5 (2H, d, C6H4CH2); 2.7-3.2 (1H, m, C6H4CH); 3.7 (2H, d, CH2O); 7.0 (4H, s, C6H4).

Workup

  1. customThe following are obtained

Sources & evidence

ORD record
ord-3d9a0fcd7b7a495cb9769b36ae25a978
Source dataset
uspto-grants-1990_12
Patent number
US04980291

Reaction notes

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