Hydrogen Bromide → 1-Hydroxymethyl-2-(1'-bromoethyl)-benzene

HRID 1703192Notes

Reaction equation

HRID 1703192 reaction equation
C1(=O)OC(=O)C2=CC=CC=C12.CC(C(O)=O)C(O)=O.O=[C:21]([C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](O)=[O:27])[CH2:22]C.OCC1C=CC=CC=1C(O)CC.OCC1C=CC=CC=1C(O)C.[BrH:56]>ClCCl>[OH:27][CH2:26][C:25]1[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=1[CH:21]([Br:56])[CH3:22]

Participants

8

Reactant 6

HCID 260Hydrogen BromideHCID 487Methylmalonic AcidHCID 6811Phthalic AnhydrideHCID 753842-Propionylbenzoic acidHCID 5769111-(2-(Hydroxymethyl)phenyl)ethanolHCID 122580001-(1-Hydroxypropyl)-2-hydroxymethylbenzene

Product 1

HCID 205236581-Hydroxymethyl-2-(1'-bromoethyl)-benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Similarly prepared from phthalic anhydride and methylmalonic acid were 2-(1'-oxopropyl)benzoic acid and thence 1-hydroxymethyl-2-(1'-hydroxypropyl)benzene (both as oils). (b) (i) 1-Hydroxymethyl-2-(1'-hydroxyethyl)benzene (10 g) was dissolved in dichloromethane (200 ml) and was saturated with hydrogen bromide gas. The solution was stirred for 2 hr. and volatile materials were evaporated to give 1-hydroxymethyl-2-(1'-bromoethyl)-benzene as an oil. Thionyl chloride (30 ml) was added to the oil and the solution was stirred for 1 hr; evaporation of thionyl chloride gave 1-chloromethyl-2-(1'-bromoethyl)benzene which was used immediately. (ii) Similarly prepared from 1-hydroxymethyl-2-(1'-hydroxypropyl)benzene were 1-hydroxymethyl-2-(1'-bromopropyl)benzene and thence 1-chloromethyl-2-(1'-bromopropyl)benzene (both as oils).

Workup

  1. customand volatile materials were evaporated

Sources & evidence

ORD record
ord-6a2a2d90c55b4923bead711b96cdac97
Source dataset
uspto-grants-1982_09
Patent number
US04351842

Reaction notes

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